The present invention relates to maltol-2-methyl pentenoates and novel compositions using such maltol-2-methyl pentenoates to augment or enhance the flavor or aroma of foodstuffs, chewing gums and medicinal products.
There has been considerable work performed relating to substances which can be used to impart (or enhance) flavors to (or in) various consumable materials, e.g., foodstuffs, medicinal products and chewing gums. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product. Sweet, strawberry-like, fruity, red berry, green, winey and cognac-like aromas as well as sweet, fruity, strawberry, berry and winey tastes are particularly desirable for many uses in foodstuff flavors, medicinal product flavors and chewing gum flavors; particularly strawberry flavors, raspberry flavors, wine flavors and cognac flavors.
U.S. Pat. No. 4,000,327 issued on Dec. 28, 1976 describes the use in berry fruit flavors of a synthetically produced 6-carbon carboxylic acid ester-containing composition comprising as its major constituent a cis-ester of 2-methyl-3-pentenoic acid having the structure: ##STR3## wherein R is one of ethyl, isobutyl or n-hexyl.
U.S. Pat. No. 3,499,769 issued on Mar. 10, 1970 discloses processes for imparting a fresh fruity flavor (particularly strawberry flavor) to foods by adding a small amount of 2-methyl-2-pentenoic acid to the foodstuff. In U.S. Pat. No. 3,499,769 it is emphasized that the basic nuance imparted by 2-methyl-2-pentenoic acid is a "berry" flavor.
Maltol, having the structure: ##STR4## is well known for its use in strawberry flavors. It is described by Arctander, "Perfume and Flavor Chemicals (Aroma Chemicals)" at number 1831 to have a warm fruity, caramellic-sweet odor with emphasis on the caramellic note in the dry state. Solutions of maltol are indicated by Arctander to show a pronounced fruity, jam-like odor of pineapple, strawberry types. Arctander further states that maltol is "intensely sweet, fruity, jam-like, . . . having a pineapple, strawberry type flavor with caramellic undertone". It is stated that the caramellic effect is predominant at high (20-100 ppm) concentrations while the fruity effect is most attractive at much lower concentrations. It is stated by Arctander that the main use of maltol is in flavor compositions not only as a fruity component in pineapple and strawberry, but in general, as a sweetener.
In addition, maltyl esters of alkanoic acids are known as flavorants. Thus, on the GRAS list (generally recognized as safe by the Flavor Extracts Manufacturers' Association) maltyl isobutyrate (number 3462, Food Technology, August 1975, page 72) is set forth. On that same page, 2-methyl-3-pentenoic acid is set forth as number 3464.
U.S. Pat. No. 2,766,148 issued on Oct. 9, 1956 sets forth the improvement in the flavor and aroma of tobacco by addition thereto of from 0.01 up to 1.0% of esters including maltol-3-methyl-valerate.
None of the prior art however sets forth compounds having structures related to the maltol-2-methyl pentenoates of the present invention. Furthermore, the properties of the maltol-2-methyl pentenoates of the present invention, from an organoleptic standpoint, are considered to be unobvious, unexpected and advantageous with respect to the organoleptic properties of the esters of the prior art set forth above.